The purpose of this paper is to reveal how the thinking of leadership is always in 'play' enacting the wisdom of practice. The 'know how' of leadership theory (techne) tends to assume that a plan, or a set of skills, can accomplish whatever one sets out to achieve. However, the nature of human and contextual encounter instead draws one into a dynamic relationship where all is in-play. To lead is to recognise the impact and primacy of play and to respond accordingly. For this research study, experienced leaders were interviewed and data was analysed drawing on the philosophical notions of Heidegger and Gadamer, using a phenomenological methodology. The findings indicate that 'know how' is not sufficient. Strong leadership requires wisdom that is enacted in the moment. In addition, 'who' the leader is matters, for in the dynamic of play leaders can only draw on their own integrity. Being attuned to the play also matters, for discerning mood, possibilities and threats prompt the leader's next move. Leadership that enables individuals to play with wisdom, foresight and sound judgement can only be learnt through experience. The implications are that emerging leaders need to be exposed to the play of leadership and to be mentored by experienced leaders who can share their wisdom.